Water → HCID 86756322, compound

HRID 568276Notes

Reaction equation

HRID 568276 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH2:17][C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[CH2:15][C@@H:14](OS(C)(=O)=O)[CH2:13]1)=[O:11])[CH:7]=[CH2:8].O>CN(C=O)C>[C:1]([S:3][C@H:14]1[CH2:15][C@@H:16]([CH2:17][C:18]2[N:19]3[CH:25]=[N:24][CH:23]=[C:20]3[S:21][CH:22]=2)[N:12]([C:10]([O:9][CH2:6][CH:7]=[CH2:8])=[O:11])[CH2:13]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 86756323HCID 86756323, compound

Product 1

HCID 86756322HCID 86756322, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium thioacetate (365 mg) is added to a solution of 427.7 mg of (3R,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-3-yl)methyl-3-methanesulfonyloxypyrrolidine in 4.5 ml of DMF, and the mixture is stirred under an argon stream at 70° C. for 8.5 hr. The reaction solution is cooled, water is added thereto, and the mixture is extracted four times with ethyl acetate. The organic layer is washed once with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The solvent is removed by evaporation under reduced pressure to give a crude product which is then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 374.7 mg of the title compound as a brown viscous material.

Workup

  1. temperatureThe reaction solution is cooled
  2. extractionthe mixture is extracted four times with ethyl acetate
  3. washThe organic layer is washed once with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed by evaporation under reduced pressure
  7. customto give a crude product which
  8. customis then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0e02260bf0e042c0b23f6a30bd2b698a
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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